The Front-to-Back Challenge

“You keep writing about this pain/pleasure mix up in your head.  That the two play off each other so well and that it’s so much fun.  I mean, sure you don’t SAY it’s so much fun in the moment, but the fact is, it keeps coming up.”

You’re sitting there, looking at me for a response.  I’m never quite sure if I should jump into things with both feet or hold off to see what you have in mind.  I mean, has anyone read the Scrabble chronicles?  Seriously.  I nod.

“So, we get to test it.  Plain and simple.  Today, I give you permission to have an orgasm.”

I grin.

“If you can.”

I stop grinning.  “What does that mean?”

You start explaining again as you pull out the wedge pillow and put it on the bed.  That curvy little smile is back.

“Well, today you’re in charge of the front.  Of making yourself cum.  But I’m in charge of the back, and stopping you.  We’ll see who wins,” you tell me.  I offer to declare a victor right now, but you’re having none of that.  “You even get a couple of warm-up edges for my entertainment.  Let’s get started, shall we?”

I lay down on the bed and am immediately re-positioned in the infamous head down, ass-up position over the wedge pillow.  It’s not too bad, but I object anyway.  You just start laughing and grab me by the now obvious handle.  “Yes, tell me how much you object.  Please.”

In very little time I’ve managed to get myself nearly off and to the edge a few times.  It feels great of course, frustrating, but great.  Part of me wants to declare victory and just push it over the top.  But of course the reprisal would be… painful.

As soon as the 2nd edge is starting to subside, I hear you declare “let the games begin…” followed by the swoosh of your crop and the connection with my ass.  The sting is remarkable and followed quickly by two more.  Then you remind me the actual goal is to have an orgasm, not squirm around the pillow trying to be “comfortable.”

My only thought is try to get myself there as quickly as possible to make the hits stop.  So I go for it.  For some reason, you’re not doing anything.  I can feel my body switching from pain avoidance to pleasure, I’m thinking you’ve let me off the hook.  But as I close my eyes to hunt down that long-overdue orgasm, I’m pulled back in an instant by 4 more solid hits of the crop, followed with “I don’t think so…”

You’re right – it jolts me back and pulls everything up by the roots in terms of any orgasm.  My brain, my body, my ass, my cock, they all seem to conspire to do these backflips – it’s hard to describe, it’s like a bad video game where the villain comes from one direction, then another shows up behind you to trick you.  Yep, that’s what’s happening here.  My body is flipping back and forth, fun, amazing, orgasmic pleasure happening out front, sharp, stinging, hot impacts going on any time it gets too good.

I try this several times, trying to ignore the impact that is coming, and trying to sneak it past you.  I finally figure out that you’re letting it build up, then slapping it back with the ultimate bitch-slap.  It’s a  good plan, if you were simply just continuing to connect with me, I’d never have a chance.  This way I get (false?) hope.

Finally I can feel myself gaining some endurance and tolerating the hits a little bit more.  I sense that they’re getting harder, but I’m getting more ok with it, and making heading trying to chase down my own orgasm for you.  The wait this time is longer and I feel my body cascading into this orgasm, no hits, just that rolling amazing, incredible nervous system rush that focuses every fiber of your being on your cock and what’s about to happen…

I give in entirely to the feelings and actually feel myself relax letting it was over me.

But of course, that’s your cue.  You see this.

SMACK!  You’ve switched implements now.  A certain wooden paddle given to you is your weapon of choice now – much broader impact, very hard, unforgiving. The sting and heat is instant and broad – both cheeks sing out with this and the next couple of hits that immediately follow.

My orgasm runs for the hills and I madly try to chase after it, without curling up into a ball from the backside torments.  You’re rubbing my ass now, “soothing it” you’d say.  But the fact is it feels a bit like you’re rubbing sandpaper on me, it’s adding to the heat that is there, exuding.  “What a gorgeous reddish-purplish hue you have going on there…”

I go back to working up to the orgasm again, bent on surprising you and getting it past, actually winning for once.  I try to give zero physical feedback on the feelings – which have turned into pure, raw emotion with the physicality of the game, and try to get to the orgasm as quickly as possible.  I feel it welling up, but I don’t change anything.  I feel it building, growing from every corner of my body and rushing to my groin, as if everything is working together to sneak the incredible orgasm out.

I feel it welling up in me, and actually feel it rushing out – firing off all of those incredible nerves that make orgasms so wonderful, so amazing. I feel every drop fighting to get out and… just as the first drop gets to the tip of my cock, you land 6 consecutive smacks with the wooden spoon, my nemesis.

I cry out in pain and pleasure, all at once.  If I didn’t know better, I’d think I would blow a gasket and be nothing left but a pool of… something.  But you stop, just as you giggle just a bit and start rubbing me again.  You’re inspecting your work.

“Very nice.  I’ll have to be a bit more observant next time.  I think mastering a spanking-ruined orgasm might be a fun goal!”

I slump over onto my side and look at you – your successful Domme smile on full display.